Jack

"Race do I look okay?" You ask Race, your bestfriend, as you got ready for your first date with Jack. You were super nervous because you've had a crush on Jack for awhile now

"Youse look great (y/n)!" Race said taking the cigar out of his mouth

"Thanks Race. I hope you ain't lyin" You said with a smile

"Nah would I lie to ya?" Race asked. You just rolled your eyes as Race laughed. You heard a knock on the door leading to the room with the bunk beds that you and Race were in

"Ready (y/n)?" Jack asked as he opened the door and extended his hand out for you to grab

"Yes I am" you said grabbing his hand

"Youse better not hurt her Jack or ya got me to deal with" Race said before we left the room

"Don't worry Race. I won't" Jack said smiling down at you

You two left the lodging house and started walking towards Tibby's. It was a beautiful day out which made this moment even more special. You two made small talk as you finally arrived at Tibby's

"Ladies first" Jack said as he opened and held the door open for you

"Thank you" you said smiling at him. You guys sat at a small table and ordered your food

"You look beautiful like always" Jack said which made you blush and look away

"Aw don't hide that gorgeous smile" Jack said causing you to blush even more if that's possible. You turned back to look at him and he was smiling at you. That smile have you butterflies in your stomach which was a good thing

You were served y'alls food which you tired not to order too much since Iyou know Jack doesn't have much money but he still told you to order whatever you wanted. During the meal you guys shared laughs and stories. You didn't ever want this date to end

"Could we have one milkshake please?" Jack asked the waiter who wrote it down on his notepad and nodded

"Oh Jack you don't have to get us one. You've already bought us our food." You said feeling a little guilty

"No it's alright, love. Don't worry bout it" Jack said grabbing your hand

"Thank you so much for today Jack it was amazing" you said smiling

"I'm glad you enjoyed it. I've wanted to take you out for awhile now but I never k ew how to ask but I'm glad I finally got the courage to" Jack said. You stared into his eyes as he did the same. They flickered to your lips as Jack leaned down to kiss you. Your lips were not even a centimeter apart before the waiter came back with the milkshake

"Oh thank you" Jack said leaning away from you as you did the same. There were to straws in the milkshake so Jack took one while you took the other. You took a sip and was amazed at how good it was

"Wow this tastes great!" you said as you continued to drink more

"Slow down there. Don't want a brain freeze" Jack said with a chuckle. You leaned back and let out a small chuckle as well. 

"Um (y/n) there is somethin I've been meanin to ask ya" Jack said looking at his hands

"Yes?" You asked a little concerned

"Um..Will you be my goil?" Jack asked looking into your eyes

"Yes, definitely " You said as you gave Jack a huge smile. Once Jack heard your answer a smile grew on his face as well

Today was one of the best days you have ever had

David

"Wait (y/n), before you go just remember if he hurts ya in anyway he'll have somethin comin for him" Jack, your older brother said. You were going on a date with his best friend so of course he was going to be very over protective

"Don't worry Jack, I'll tell him you said that" You said before walking out of the lodging house. David told you to meet him at the beach which wasn't too far plus it was summertime so it's not too cold. He said it was a surprise so your hoping hes right and this isn't a prank or anything. You finally made it to the beach and started looking around for David. You walked down the beach whenever you saw a heart made out of candles surrounding a table with two chairs. You thought it was adorable and whichever girl got this sure was lucky. Thats when you felt arms go around your waist making you freeze

"Don't worry doll, it's just me" You heard David said making you relax again

"Isn't it pretty?" David said again after a moment of silence

"It sure is. Whichever girl gets this is really luck" You said turning around to face David

"I'm glad you think that because this is for you" He said with a smile making you gasp

"Really?!" You asked excitedly

"Of course. Only the best for you" David said before you tackled him into a hug

"Aww David. This is the best thing anyone has ever done for me" You said getting a little emotional

"Come on" David said grabbing your hand and leading you to the table. He pulled the chair out to let you sit then went to the other chair and sat down. You took in the beautifulness of everything and just smiled

"Your smile is adorable" David said 

"Thank you" you said blushing. David reached across the table and grabbed your hand rubbing it with his thumb

"I'm so glad that I get to be here with you. I've liked you for awhile and was nervous to ask you out on a date since your brother is Jack. I didn't think he would allow this but I'm so happy that he did" David said smiling at you

"I'm so happy he did too. Before Ise left today he told me that if you ever hurt me in anyway you'll have somethin comin for ya" You said with a small laugh

"I would never hurt ya" David said laughing as well

"In fact I have somethin to ask you" David said starting to seem a little nervous now

"What is it?" you asked

"Would you be my goil?" David asked 

"of course" You said with a smile making David smile as well. You spent the rest of the night with David and you wouldn't have wanted to be anywhere else

Spot

"He'll be here soon" Mush, your brother, said walking into the newsies' room where you were at. You were getting ready for your first date with Spot. You've been talking to Spot for awhile now and he finally asked to take you on a date. You were super excited and nervous because well it's Spot Conlon, King of Brooklyn.

"Okay, thank you Mush. Does my hair look okay?" You asked while looking at yourself in the small mirrors in the bathroom

"It look beautiful. He'll think yous look beautiful as well" Mush said giving you a reassuring smile

"You really think so?" 

"Ise know so. Just don't do anything Ise would do" Mush said giving you a wink. You laughed as you knew exactly what he was talking about. Mush is known as a womanizer so it's not too hard to guess what he is talking about

"Don't worry Mush. Ise wont it's only the first date. That is for the second date" You said giving him a wink back. He gave you a disgusted face making you laugh

"I hope youse kiddin" He said trying to give you a serious face

"You know Ise am Mush....or am Ise?" You said. You loved making your brother uncomfortable but obviously he didn't

"Okay well I'm gonna go downstairs. I'll let ya know when hes here" Mush said as he exited the room. You looked at yourself in the mirror and smiled. You couldn't believe you were going on a date with the King of Brooklyn. You've heard many things about him being a womanizer but you didn't believe them. Spot has been so nice to you. It seems like your the only person he is nice to, everyone else he's someone they fear.

"(y/n) Spot's here!" You heard Mush yell from downstairs. You looked at yourself once more before heading downstairs

"If ya hurt her ya going to regret it" You heard Mush tell Spot as you made it to the last step

"I won't. I would never" Spot said as he looked at you with a smile. You smiled back as you walked over to them. You saw behind Mush was the rest of the Newsies. They were all like brothers to you so of course they had to be here too

"Be careful (y/n) and don't be home too late" Jack said from beside Mush

"Yeah and don't do anything Mush would do" Kid Blink said from the other side of Mush. That made you laugh since Mush said the same thing

"I already told her that" Mush said crossing his arms

"I'll be careful guys. Thank you" You said as Spot opened the door letting you exit first. Spot then exited as well grabbing your hand and leading you down the steps

"Where are ye going?" You asked once you reached the bottom

"It's a surprise" Spot said with a smile. You two continued to make small talk as he lead you to wherever the date was. You two walked across the Brooklyn Bridge and finally made it to a small park. In the middle was a blanket with a picnic basket in the middle

"Oh Spot, this is lovely" You said as the two you you reached the basket. You sat down as Spot sat down next to you giving you a smile

"Ise was hoping you would like it" Spot said as he opened the basket revealing all the food. In the basket was apples, bread, and cheese

"How did you get this food?" You asked knowing Spot didn't have a lot of money

"I'm the King of Brooklyn. I get what I want" Spot said grabbing two apples and giving you one. You had an amazing time with Spot as you two finished all the food and talked about many things.

"Come on. I have something else to show ya" Spot said as he stood up and reached his hand out for you to take. You took his hand intertwining your finger as you two started walking. The two of you ended up at a bench that gave you the perfect view of the Brooklyn Bridge. 

"Wow Spot it's beautiful" You said as you two sat down on the bench. You looked at all the lights shining beautifully since the sun was starting to set

"Not as beautiful as you" Spot said making you turn to look at him. He was looking at you with lust in his eyes

"I've been meaning to ask you somethin" Spot said sounding a little nervous

"Yes Spot?" You said still staring into his gorgeous eyes

"Would you be my goil?" 

"Definitely" You said smiling. Spot started smiling as well. You turned back to look as the bridge while you took in this moment. It was a moment you would never forget

A/N- I will post the other boys after this chapter. I didn't want to post all of them together I feel like it would be a lot. Sorry for not updating on here for what feels like forever. I'll try and start updating more!